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USVI 8 Day / 7 Night Sample Itinerary

Your crew will tailor each and every itinerary to your desires. There’s so much to do in the Virgin Islands and we’re here to ensure our guests get the most out of their magical week aboard their yacht. Given that weather in the islands changes quite frequently, we keep our itinerary dynamic, typically discussing options for the next day’s activities and ports of call over sun-downers each evening. Please use this sample itinerary as a jumping-off point, subject to change.

Day 1: Charlotte Amalie | Buck Island | Water Island

Arrive in the Islands at St. Thomas International Airport. Our preferred driver will receive you in baggage claim and transfer you directly to the
harbor where your captain, chef and yacht will be eagerly awaiting your arrival. After settling in on board your yacht, enjoy a quick sail over to Buck Island to snorkel with turtles and check out some cool underwater wrecks! A short sail away is Water Island, where you’ll drop the hook for the night, offering guests the opportunity to check out Dhingy’s Local Beach Bar and sink their toes in the sand. Indulge in the first of many delicious dinners by the chef,
specially catered to your tastes and preferences.

Day 2: Magen’s Bay

Wake up in paradise and enjoy a leisurely downwind sail around the west end of St. Thomas. Want to learn the ropes? Your captain is likely a sailing instructor, and would love to offer guests the chance to take the helm and learn about seamanship. Arrive in Magen’s bay, one of St. Thomas’s most prized beaches, where we’ll spend the day enjoying water sports, playing on the beach, or simply relaxing aboard the yacht.

Day 3: Hans Lollick | Grass Cay | Lovango Cay

Off to the next beautiful anchorage! After a leisurely breakfast, we’ll hoist sail and head for one of the lesser-traveled islands off of St. Thomas’s north shore. For guests looking to get off the beaten path, Hans Lollick or Grass Cay offer pristine, nearly private, white-sand beaches. For guests interested in mingling ashore, the brand new Lovango Cay Beach Club and Resort offers visitors a beautiful beach bar, 70ft infinity pool, and cabanas available for rent. Cap off the day by cozying up on the bow and stargazing!

Day 4: Caneel Bay | Honeymoon Beach | Cruz Bay

Wake up just outside St. John’s historical Caneel Bay Resort. Try your hand at paddleboarding, or request your crew to tender you in to the beautiful Honeymoon Beach to soak up some sunshine. Located just around the corner from Cruz Bay, we have an abundance of activity options for this day. Stroll around the local shops, join your crew on a hike for some of the best views of St. John’s north shore, or explore the coves by Kayak! Cruz Bay offers some of the best dining options as well, making for a perfect opportunity to indulge in dinner or lunch ashore.

Day 5: Waterlemon Cay | Maho Bay

Learn about St. John’s rich cultural history with a shoreside walk to the island’s best-preserved ruins. The Annaberg Sugar Plantation will transport you back to St. John’s hay-day of sugar production, while offering breathtaking views of the islands. Spend the afternoon snorkeling with turtles at Maho Bay (or as we like to call it, “Turtle Cove”) or belly up to the bar at Crossroads for a local craft beer!

Day 6: Coral Bay | Little Lameshur

Did somebody say floating taco bar? Yup, we sure did! We’ll set sail for St. John’s Coral Harbor. Grab your fins and swim up to Limeout, St. John’s iconic floating taco bar for lunch. Spend the afternoon snorkeling in St. John’s beautifully protected waters with your captain as your personal guide where you will experience the crews passion for wildlife and fish ID. Head back to the yacht for happy hour, tasty treats and cocktails whipped up by the chef.

Day 7: Reef Bay | Rendezvous Bay

Embark on a secret trail walk with your crew to discover ancient petroglyphs hidden within the shores of St. John. Enjoy a well-deserved lunch aboard your yacht before a leisurely downwind sail to Rendezvous Bay. This quiet, tucked away cove is a perfect spot for water sports: tubing, wakeboarding,
sub-wing, fishing, you name it! We’ll cap the day off with a special send-off dinner while reminiscing about the wonderful week aboard
the yacht.

Day 8: Final Sail and Drop off in St. Thomas

Indulge in the chef’s bloody mary bar and get one last snorkel or swim in before we sail back to St. Thomas. We’ll coordinate with our driver to ensure your transition back to the airport or on-island accommodations are seamless, and share a final toast to good times and good company. Until next time!

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